Top Chief Of Staff Jobs in Chicago, IL

Chief of Staff to the Chief Content Officer, responsible for translating company strategy into operating systems, driving planning and governance, overseeing strategic projects, enabling cross-functional alignment, supporting executive decision-making, leading engagement and communications initiatives, and improving organizational performance across the Content organization.

Serve as a strategic partner and force multiplier to the Founder/CEO. Manage executive priorities, represent the CEO, drive ELT operating cadence and cross-functional alignment, prepare leadership and board materials, lead high-impact special projects, and implement AI tools to improve productivity. The role requires exceptional communication, analytical problem-solving, discretion, resilience, organization, and the ability to operate effectively in ambiguity.

Leads strategic cross-functional projects and operational workflows for the Global Payments Network. Structures ambiguous problems into actionable plans, manages timelines and stakeholders, develops data-driven executive communications, influences decisions, and builds scalable solutions that improve associate and customer outcomes. Serves as a thought partner to leadership, supports team operations, and promotes collaboration and best practices.

Two-year executive leadership program partnering with operating leaders, CEOs, and functional teams across vertical software companies. Own cross-functional value-creation initiatives spanning go-to-market, sales, marketing, pricing, customer success, finance, M&A integration, and business operations. Support executive decision-making, implement operating improvements, and help newly acquired companies establish priorities and operating rhythms. High performers may advance into CEO, C-suite, or headquarters leadership roles.

Serve as the CEO's strategic and operational right hand at an AI LegalTech startup: prepare executive/board/investor materials, build financial models and decks, contribute litigation expertise to product content, validate LLM-generated analyses, drive cross-functional execution, manage company operations (recruiting, vendor administration, OKRs), represent the CEO, and handle special projects across finance, legal, and partnerships.

Leads as strategic partner and operational integrator to the CFO, coordinating financial planning, budgeting, forecasting, executive communications, board and investor materials, cross-functional initiatives, and Finance’s operating cadence. Drives accountability, operational efficiency, financial transformation, cost optimization, and enterprise alignment while advising senior leaders and supporting high-priority projects across Finance and the broader organization.

Serves as a trusted advisor to the Chief Commercial Officer and leadership team, driving strategic projects, business planning, executive communications, meetings, board materials, and performance reporting. Prioritizes executive agendas, coordinates cross-functional initiatives, identifies risks and solutions, facilitates decisions, and ensures follow-through. The role also supports organizational effectiveness, stakeholder engagement, and leadership development across a global commercial and medical organization.

Serves as the Chief Customer Officer’s strategic and operational partner, driving customer strategy execution, annual planning, cross-functional transformation initiatives, operating cadences, performance reporting, dashboards, and budget planning. Advises senior leaders, facilitates decision-making, coordinates executive meetings and reviews, analyzes business metrics, and leads organizational change across the customer organization.

The Chief of Staff translates organizational priorities into systems, culture, communication standards, and operating rhythms. Responsibilities include overseeing onboarding and offboarding, performance tracking, training, resilience planning, leadership communication, executive time management, meetings, strategic alignment, and cross-functional special projects. The role requires proactive problem-solving, empathetic communication, meticulous execution, and the ability to build structure in ambiguous environments.

The Chief of Staff supports executive leadership by facilitating strategy planning, executive operating rhythms, decision governance, board preparation, communications, and cross-functional initiatives. This role tracks enterprise priorities, coordinates strategic execution, prepares executive materials, facilitates senior-level discussions, and ensures decisions and action items are communicated and completed. The position requires strong influence, judgment, discretion, analytical ability, and insurance business acumen.

The Chief of Staff supports the Americas GM across sales, marketing, account management, service delivery, finance, and HR. Responsibilities include coordinating cross-functional initiatives, managing executive operating cadences, preparing communications and presentations, supporting sales forecasting and planning, driving partnerships and special projects, and providing analysis for strategic decisions. The role also supports organizational growth, talent development, budgeting, P&L oversight, customer retention, and achievement of revenue and profitability targets.

Lead strategic 0-to-1 initiatives supporting Schoolhouse’s 2028 vision, manage high-stakes relationships with partners and donors, and run the organization’s operating rhythm. The Chief of Staff will report to the President, drive cross-functional projects, improve workflows, support HR, legal, and finance activities, oversee hiring processes, and plan team retreats. The role requires strong judgment, communication, ownership, and comfort operating in ambiguity at a fast-growing nonprofit.

Serve as the strategic and operational partner to the AI and Data Transformation & Analytics Practice Leader. Own leadership cadence, strategic initiative execution, AI governance, investment oversight, FP&A partnership, pipeline and revenue enablement, communications, and change management. Coordinate cross-functional stakeholders, improve practice operations, support executive forums, and ensure accountability, financial discipline, and alignment with firmwide strategy.

Drive strategic execution for the AI Neobank: build operating rhythms, manage OKRs, coordinate cross-functional workstreams, prepare leadership/board materials, identify and mitigate risks, support trade-offs and special projects requiring senior judgment and cross-functional authority.

Acts as the CEO’s right hand, translating company priorities into operating plans, tracking owners and deadlines, analyzing commercial and operational performance, and running leadership rhythms. Owns cross-functional project delivery, process redesign, decision tracking, and executive materials. The role requires strong program management, analytical and financial understanding, influence without authority, structured communication, and independent execution.

Serves as strategic partner and force multiplier to the Chief Revenue Officer, driving revenue leadership operations, strategic planning, goal tracking, executive and board communications, customer and partner engagement, and cross-functional resolution of business priorities. The role manages CRO office initiatives, optimizes executive time, builds scalable operating processes, and coordinates with senior leaders across Sales, Finance, Operations, People, and other teams.

Leads commercial growth initiatives from concept through traction, including market sizing, business cases, go-to-market strategy, competitive intelligence, and cross-functional execution. Drives executive committee operating rhythms, board preparation, strategic initiative tracking, decision-making, and accountability across Product, Clinical, Marketing, Finance, Sales, and executive stakeholders.

Leads Waymark’s strategic planning, OKR management, executive operating rhythm, internal communications, and business process development. Partners with the CEO and executive team to translate strategy into goals, improve cross-functional coordination, manage decision-making systems, produce executive and board communications, and drive high-priority initiatives. The role requires strong analytical, communication, financial modeling, process design, and influence skills in a healthcare-focused, high-growth environment.

Support senior leaders by managing complex calendars, meetings, travel, communications, presentations, action items, and confidential information. Coordinate cross-functional priorities, prepare executives for meetings, track follow-ups, improve workflows, and support special projects in a fast-paced healthcare organization.

Serve as strategic partner to the SVP of Product to scale product leadership: run leadership rhythms, own headcount and budget planning, drive AI enablement, curate external product narrative, manage org-health metrics, and resolve cross-functional structural issues to increase decision speed and org effectiveness.

Deputy to the Chief Engineer responsible for leading engineering personnel, planning and executing maintenance and repairs, managing spares and fuel operations, ensuring environmental compliance, supporting safety investigations, and maintaining the shipboard management system and risk assessments.

Own the CEO’s calendar, follow-ups, project-management systems, hiring operations, content execution tracking, metrics, reporting, and special projects. The role protects executive focus, enforces accountability across teams, coordinates hiring pipelines, analyzes financial and performance data, and builds scalable operating rhythms. It is a high-trust Executive Operations position with a performance-based path toward Chief of Staff responsibilities.

Serve as Chief of Staff to the CHRO, managing the People leadership operating cadence, leading cross-functional initiatives end-to-end, crafting executive communications, resolving issues proactively, and representing CHRO priorities across the organization.

Serve as the Chief Growth Officer’s strategic operator, leading GTM execution across Sales, Marketing, Channel, Customer Success, Product, and Finance. Own revenue operations, pricing, deal governance, forecasting, territory and quota planning, data unification, HubSpot architecture, executive dashboards, pipeline optimization, and Q2C processes. Manage a HubSpot Administrator, improve commercial analytics, establish operating cadence, and deploy AI-enabled workflows across the GTM technology stack.

Serves as strategic partner to the President of Seramount, leading executive preparation, strategic prioritization, cross-functional initiatives, leadership operating rhythms, decision support, communications, organizational change, AI adoption, and employee engagement. The role translates strategy into coordinated execution, facilitates leadership decisions, and ensures commitments are completed across the organization.